White Shirts and Dirty Money
A Love Letter to Tokyo’s Hostess Culture and the Beautiful Chaos That Came With It
Tokyo is not a quiet place. It is a kaleidoscope of movement, color, and electric life. Even the shadows feel alive. The vending machines hum softly on every corner, glowing with strange little drinks and neon promises. Trains rattle above and below like metal ghosts. Smoke from yakitori stalls twists through narrow alleys. In Roppongi, everything smells like ambition and cheap cologne. It is loud, fast, transactional, and hypnotic. A place that seems designed to blur time, to keep you moving just fast enough that you forget to ask why you’re there.
When I was living there, I somehow ended up working as a talent scout for One Eye Jack’s bar. That was the official title. Unofficially, I wandered Roppongi trying to convince foreign backpackers to come work as hostesses in a club I could barely explain. The whole thing felt off from the beginning. There was the moral ambiguity, the absurdity of the task, and the simple truth that I was painfully shy. Not ideal for someone hired to approach beautiful strangers and sell them on a dream wrapped in red velvet and false promises.
So I mostly wandered.
I spent that first week circling Roppongi Crossing and its maze of side streets. Camera in hand, playing tourist. I watched the rhythms of the place. Men in suits weaving through traffic. Girls in heels texting furiously. Barkers pitching clubs behind mirrored sunglasses. I’d clock in around five or seven, walk until midnight, and clock out. I wasn’t recruiting anyone. I wasn’t even trying.
As the nights turned colder and the damp settled into my bones, I started drifting further. I’d clock in at the bar, then quietly head back to the flat to hang out with LK. She’d usually get home around seven, and until then we hadn’t had much time to connect. We’d split a drink, share a laugh, and I’d walk back out into the neon wash to clock out, pretending I’d done a full night’s work.
That little scheme lasted four nights.
On the fifth, the head scout was waiting for me. He asked where I’d been and why I hadn’t brought anyone in. I fed him a line. He saw right through it. He told me if I was going to slack off, I should at least do it at the scout bar where the others went to stay warm. I wish I could remember the name of that place. It felt like just another bar then. But what happened there set something else in motion. A step, maybe, toward something bigger. Not destiny. Not fate. Just the moment you realize you’ve crossed into a different part of the story. The trajectory of my life changed in that bar. We will explore that as well.
Not long after, the bosses pulled me off the streets. They told me to buy a white shirt and start working inside. I became a floor waiter at the club. Keep the tables clean. Keep the drinks flowing. Keep the ashtrays empty.
That was the job.
For context, the only “Jason” most Japanese people seemed to know was the one in the hockey mask from Friday the 13th. So every time I introduced myself, I got the same reaction. A dramatic, guttural “Oooooh,” followed by some air-stabbing pantomime. Every single time. It was weirdly endearing.
The foreign hostesses were a tougher crowd. Cold, sharp-edged, uninterested in bonding. I kept my distance. The Japanese hostesses, though, were different. Curious, funny, and surprisingly open. A few asked about California. We swapped stories. Inside jokes started to form. Eventually, I became close with two of them. They were nothing like the stereotype. They were wild, clever, goofy in the best possible way.
My nights began to take shape.
Clock in at seven.
Wipe tables. Stack glasses.
By nine, the clients rolled in. Suits and Rolexes. Gold lighters. Cigarette smoke. Soft voices making sharp requests.
By midnight, the dance show. Velvet curtains. Thumping bass. A shift in the room’s temperature. By 1:48 AM, the place was soaked in alcohol and blurred intention. Clients trying to convince hostesses to hit a love hotel or tag along to some afterhours spot. Some went. Some didn’t. Depends on the girl. Depends on the night. Depends on the financial offer.
Most nights, I’d leave with Chris, a waiter from Wales, and a couple of the Japanese hostesses. We created a little gang. We’d walk the city together, following glowing signs and empty streets to whatever latenight Denny’s knockoff we could find. Pancakes. Omelets. Cigarettes. Endless water refills. We’d laugh until the energy wore off and that strange predawn stillness set in. The kind where Tokyo starts to exhale. Then we’d wait at the station for the first train so the girls could head home. I lived close enough to walk. My shoes echoing against the empty sidewalks, the whole city holding its breath before the next day rushed in.
Eventually, the two hostesses I was closest with shared their real names with me. In a world of stage names and curated personas, that was no small gesture. That was real. That was trust.
Years later, they came to visit me in California. It was the first time I had used a dishwasher and had flooded a rental apartment in SF. It was a blast.
Next time, I’ll take you along on one of those nights a dohan with my Japanese hostess friends and their wealthy clients that started with pasta and ended with glass coffins, candlelight, and one very awkward proposition.
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LOVE & LIGHT
MM